


The Wandering Sapphire

by JHTR



Category: Critical Role (Web Series)
Genre: Anal Sex, Blow Jobs, Bondage, Cunnilingus, Double Penetration, F/F, F/M, Facials, Knotting, Knotting Dildos, Multi, PWP without Porn, Pegging, Praise Kink, Sex Toys, Size Difference, Size Kink, Tail Sex, Threesome - F/F/M, Work In Progress
Language: English
Status: In-Progress
Published: 2020-03-29
Updated: 2020-09-14
Packaged: 2021-03-01 01:21:51
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 9,799
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23376832
Author URL: https://archiveofourown.org/users/JHTR/pseuds/JHTR
Summary: Jester is The Wandering Sapphire, a traveling courtesan slowly gaining reputation to rival The Ruby of the Sea. The Sapphire’s curiosity carved out a niche among more adventurous clients.
Relationships: Allura Vysoren/Jester, Allura Vysoren/Kima/Jester, Kima/Allura Vysoren, Kima/Jester, Percival "Percy" Fredrickstein Von Musel Klossowski de Rolo III/Jester, Percival "Percy" Fredrickstein Von Musel Klossowski de Rolo III/Vex'ahlia, Percival "Percy" Fredrickstein Von Musel Klossowski de Rolo III/Vex'ashlia/Jester, Vex'ahlia/Jester
Comments: 8
Kudos: 55





	1. The Del Rolos

**Author's Note:**

> This is an AU. Campaign 1 is 100% canon but Campaign 2 is not. I basically just wanted a PWP scenario where Jester interacts with characters from both campaigns (most of the Mighty Nein are probably traveling with Jester, such as Beau and Yasha being her body guards, Fjord being captain of the ship she travels on etc.). Also, as I feel the need to address this, I do not think Marion will disapprove of this life for Jester. Neither one of them were ashamed of what Marion did. Also, I do not own Critical Role (unsure if this disclaimer is needed here but figured it's pretty standard) or make money off of this fic.

“Happy anniversary, darling.” Lady Vex’ahlia de Rolo smiled at her husband.

“Happy anniversary, my dear Vex’ahlia. Gods, has it been 25 years already?” The couple was finally alone in Vex’s mansion after the obligated parties with family, friends, and diplomats. “I am so glad we can just come here to get away from all that. Just the two of us. None bustle of the castle.”

Vex smirked at that. “Well, actually I’ve arranged for some company tonight.”

“Oh? And who will that be? I didn’t notice Zahra and Kash at the party, although if you were keeping them a secret…” There was a look of excitement beneath the surface of Percy’s usual dry expression. Vex recognized it.

“Actually, I’ve sent a request to the Lavish Chateau. I know how much you’ve enjoyed our trip there.” The dark haired half-elf giggled at Percy’s blush. “Not that I had any complaints.”

Percy fiddled with his glasses. “Yes, well it was your idea. But I was under the impression The Ruby of the Sea didn’t leave Nicodranas?”

“She doesn’t. But her protégé does.”

“Courtesans have protégés? How does one get that job?”

“Looking for a new career, darling?” Vex grabbed Percy’s hand. “Well The Wandering Sapphire should be waiting in the bedroom.” The white haired Lord of Whitestone followed the Baroness of the First House of Whitestone and Mistress of the Grey Hunt into the bedroom. He felt at home here despite living in the castle. This is where they came to escape their titles.

Jester waited on the bed as her clients entered. She smiled. It was show time. “Welcome, Lady Vex’ahlia de Rolo. And Lord Percival Fredrickstein von Mussel Klossowski de Rolo The Third. My pleasure to meet you.” The blue skinned tiefling walked up to the husband and wife. “I hope you like my outfit, My Lady. Ma--- The Ruby of the sea didn’t say anything about preferences you guys had for clothes so I took the liberty of picking something on theme for your other requests.”

Percy could imagine what Vex had in mind. The blue girl in front of him was dressed in all black. She wore a tight bodice that showed plenty of cleavage with extra belts and buckles. It flowed into a black dress. The ends appeared tattered, as if she ripped it herself. A pair of black leather high heeled boots, black lipstick, and a chain from her earring to the horns completed the look. The only things that distracted from the medieval dominatrix look was a pink backpack flung over her back and the unicorn tattoos on her bare shoulders.

“O, darling. You look wonderful. Although you seem to be packing light.” Vex looked around the room searching for some items she requested.

“Ah yes. Don’t worry, Lady Vex’ahlia. I have everything we need. This haversack is deceptively roomy.” She patted the pink backpack. “But first, we need to go over safe words and limits. I personally suggest something silly that would kill the mood but not too much. Like Hupperdook. I’ve had a client who used an ex lover before but that didn’t turn out too well. I ended up spending the rest of the session stroking her hair while she cried.” Jester saw the awkwardness on the faces. “Not that I’ll ever reveal their identity or judge them. Trust me, that isn’t the worse thing I’ve seen. But where were we? O yea, safe words. I believe you’re the one who would be using it Lord de Rolo, although you might want one too Lady Vex’ahlia.”

Vex tried not to laugh at how bubbling the courtesan was. But she noticed how at ease Percy was among the humor. And she was too. “Please, call me Vex. And that’s Percy. And what may we call you? The Wandering Sapphire seems a bit formal.”

“O yes. My name’s Jester. So, Percy, have a safe word yet?”

Percy walked over to the bed and sat down. “Victor.” Vex gave him an expression he hasn’t quite seen before. It was close to whenever Grog has done something dumb. “What, she said something silly and will kill the mood. Trust me, it qualifies. You got a better one?”

“Well, I was thinking ‘Life needs things to live’ if I need one.” Percy just sighed at that reminder. “So what’s next, do we take off our clothes now?”

Jester sensed the history between the two. They had more shared experiences in a human life time than most elves and dwarves could ever hope for. She smiled “Not yet. We still need to go over what you both want, what you are comfortable with, and what you don’t like. And of course if there is anything I need to avoid. Especially you, Percy, as your wife was the one who contacted The Lavish Chateau.” She took out a handwritten list. “Let’s see, some bondage for Lord de Rolo, some sensual loving for Lady Vex while her husband can ‘do nothing but squirm until his cock is so painfully hard and desperate for release he is begging to sign away Whitestone just to cum’ (my, you do have a mind for this Vex) and some pegging to wrap things up.” At Percy’s blank look she explained. “It’s where a girl fucks a guy with a toy. Mm, now that does seem like fun. Now, is there anything you want to add or avoid? Could be anything from how you want me to talk to you to any sex act not on here or whatever. Or any pet names I should know about.”

Percy thought about that for a moment. Overall there was nothing really new on the list. Although there was something not mentioned directly. “I call Vex by her title at times in bed. Especially when she’s tying me up. And um, compliment me when the opportunity arises.” He watched Jester write down “praise kink” with a check next to it. Percy never knew it had a name, but it seemed to fit. Vex certainly didn’t need encouragement to bring that in. “And avoid belittling and degrading talk. Zahra tried that once and it ruined the mood.” He thought more about some awkward times. “And while I like bondage, please avoid pain. Not all of it, any physical activity is going to bring some layer of pain but no rough spanking, drawing blood, whips or anything like that.” Jester wrote something else down and drew a line through it.

Percy was surprised that Jester didn’t ask for an explanation. He expected to have to explain the torture he suffered at the hands of the Ripley and the Briarwoods. “Also, Vex likes the tiefling antimony.” Both women looked at him like a college professor talking about sex. “I mean, she likes it when a tail rubs against her body and caresses her or when you nibble her neck with fangs.” The tiefling scribbled that down.

“Mm, yes I do darling. Thanks for remembering.” Vex kissed him on the cheek. “So, are we ready, Jester?”

The tiefling fumbled through her backpack in search of what she needed. “One second, just taking out the fun stuff. Mm, I think silk will do.” She pulled out some rope alongside a leather harness, a small bottle and a few dildos. “So, do either of you have a size preference?”

Percy spoke first. “You can choose, dear. You know what I like and can handle more than I do most days.”

“The pink sparkly one” Vex answered immediately.

“Ah, my favorite. Trust me, you’ll love Spinkles.” The blue woman smiled at Percy before putting the other toys away. “So shall we begin?”

Percy nodded. “At your leisure.” He began unbuttoning his jacket.

“Stop, darling. Let us do that.” Percival stopped immediately at his wife’s order. The two women approached.

“Such an obedient boy. O, this is going to be so fun.” Jester unbuttoned his jacket next. She gave him a quick kiss on his cheek. “Arms up.” She removed his jacket and shirt. “Normally I’ll just rip these off, but you look so tasty in them. It’ll be a shame to ruin such a regal look.” As she folded the clothes Vex took off Percy’s pants.

“On the bed, darling.” Jester passed Vex’ahlia some rope. “Thanks, Jester. I’ll take his legs while you get his arms.”

Jester giggled and went to work. She tied one of Percy’s hands to the bed post. “Is that good, Percy? It isn’t too tight is it?” Percy nodded. “I need you to speak to me, please. Cutting off the circulation could lead to losing an arm.”

Percy chuckled. “Well, won’t be the first time. But no, that’s perfect, Miss Sapphire.” He moved his arm slightly.

“Miss Sapphire? Mm, I quite like that. I’m a bit too young to go by ‘madam’ I think.” Jester climbed onto the bed and straddled Percy’s bare chest. “Other hand, please.” She tied the other arm while still on top of Lord de Rolo. Then Jester lowered herself down to kiss him. As soon as he began to kiss back she stopped and started kissing his neck.

“O gods” Percy moaned. He was completely tied to the bed now. Jester sucked on his neck while she pumped his cock with her hand. He didn’t even realize she grabbed it. He moaned and tried to thrust into her palm.

Vex noticed. “No moving, Percy. Or else I’ll just have to take this cutie to another room and leave you here. Isn’t she sexy? I think she’s sexier than The Ruby of the Sea, don’t you Percival?”

“Yes, Lady Vex’ahlia. More beautiful by far.” Percy’s breathing was labored. Jester still massaged the cock.

Jester backed off from his neck. It was already red. “And will you be saying that without your cock in my hand? Besides, The Ruby isn’t here. There’s no need to compare.” She crawled off the bed and left his cock. “Such a good boy, and such a pretty cock. I’m going have fun with you later. But for now…” She bounced over to where Vex was. “So, do you want a mark to match your husband’s?”

“Fuck yes.” The half-elf grinned and pulled the courtesan into a kiss. The kiss was longer and deeper than the last. Jester allowed Vex to enjoy it for a bit. Jester nibbled at Vex’s lip. The older woman whimpered into the blue lips. Her dress came off without the kiss breaking.

Jester moved to Vex’s neck while still undressing the Lady of Whitestone. Vex moaned as the little fangs dug into her. It wasn’t enough pressure to break the skin, but Vex knew it’ll leave a mark. “O darling, don’t you think I’m a bit old for hickies?”

“Please, you’re not that old Vex. Trust me, I’ve had much older.” She giggled at the memories. Then seeing Vex about to respond “and not just elves and dwarves. Besides, even if you are an old married couple, you’re a sexy old married couple. Trust me, Lady Vex’ahlia, you’re a certified milf. And I’m sure that with that age comes experience none of the blushing virgins I see have.” She emphasized the point with a hard suck against Vex’s neck. “I hate teaching. And I’m sure you know how to cover love bites with make ups and scarves. It is a bit chilly up here.”

“O darling, you’re good.” Vex meant that. Both the flattery and the foreplay were excellent. She shuddered as the blue horned woman went lower.

Jester sucked Vex’s nipple into her mouth. Vex breathed harder. The blue tiefling smirked then quickly brushed her fangs across the nub. “Do you like this, Vex? Want me to play with your titties? They’re so fun.” Jester’s mouth moved between each breast. “I could do this for hours.”

“Fuck, don’t you dare.” Vex grasped Jester’s horns. “I’m not as patient as my husband.” She looked over at him. “So, darling, enjoying the show?”

“Pelor, yes. You’re so beautiful. Both of you.”

“Your husband is such a flatterer. So, time to step things up?” At Vex’s nod Jester dove between her legs. “So, you want it fast, right?” Another eager nod had Jester’s tongue inside the half-elf. “I knew you’ll be sweet.” Jester’s words went unheard. Vex’s legs locked around her head and muffled any sound.

“O yea, faster please. Yes, please, more. Just shove that blue little tongue into me and fuck my brains out.” The tiefling happily obeyed. “O, darling, she’s fucking amazing.”

“I can see that.” Percy’s cock was painfully hard.

Vex tightened her grip on Jester’s horns and shoved her face deeper. She screamed out an orgasm. Jester continued sucking and licking until Vex spoke again. “Sweetie, you’re so good. But I think you need a reward.”

The traveling concubine kissed her way back up Vex’s body. “And how do you want me, Lady Vex’ahlia”? Her face glistened.

“Up. And finish undressing.” The Sapphire did so. Not quite a strip show, but enough to draw the attention of both Whitestone rulers. As she did so, Vex grabbed a blanket and a pillow. She set up a makeshift bed and lied down. “Now, I want the Wanderign Sapphire to sit on my face tils he gushes all over me.”

“Well, only fair to return the favor.” Jester moved over and lowered herself. She faced Percy as she did so. “So, how hard should I ride your wife’s face?”

Percy took a second to realize he was supposed to answer. “Start slow. Let her tease you, she’s a master at it. Even if she doesn’t have the patience for it herself”.

Before Vex could retort Jester lowered herself down. “Mm, yes she seems quite skilled.” Vex slowly licked at Jester’s folds. Vex moaned into Jester as she felt something rub across her breasts. It took her a moment to figure out it was Jester’s tail. The blue skinned woman continued to rub the half-elf’s body with her tail.

The more Jester moaned, the faster and lower her tail moved. “Lady Vex’ahlia, I’m going need you to listen, ok? I want you to tap my butt with 3 fingers. Can you do that?” Vex did. “Good. Now if anything I do is too much for you or doesn’t feel good or make you uncomfortable, just tap me like that again.” She paused for the message to get in. “Now, Vex, you are going to continue eating me out like I’m you favorite cupcake. Maybe blueberry, or black moss flavor. But when I start fucking you with my tail, I want you to go faster and faster as I fuck you. Is that ok with you, darling?” Jester lifted herself up just long enough to see the half-elven woman nod.

Vex was so focused on tonguing out the younger woman on top of her that she almost missed the tail teasing her own lips. The sudden cold though caused her to gasp. But she adjusted and soon she was in sync, moving her tongue just as fast as the tail.

“So, Lord Del Rolo, have your wife ever been tail fucked?”

“Never, Miss Sapphire. But I’m sure she’ll enjoy it.” Percy loved the view. “I’ll have to tell Zahra and Lilith about this trick.”

“Just be careful, and use lube for the first time. Although your wife is so wet and sloppy I don’t really need it. Plus I know what I’m doing.” Jester’s tail dipped a few inches in. “ So tell me, should I give this little tease a taste of her own medicine, or should I give her all I got?”

Percy didn’t hesitate. “Give her all you can.” Vex knew he would, he never denied her anything she wanted. Jester’s tail began going in and out of her. Slower than she wanted, but more. The feeling was weird, but pleasant.

Vex kept up her end of the bargain. Her tongue went deeper and deeper as the tail did. Soon it was pistoning in and out of Jester. The tiefling moaned louder and louder. She was unable to speak out her next direction, but it didn’t seem needed. She pumped her tail a bit quicker into Vex’s cunt at the same time Vex moved her hands to start fingering the tiefling. “Naughty girl, but keep going.” The two women came at the same time.

Jester fell off of Vex’s face and quickly slid down to cuddle and caress. Once she regained herself, she pulled herself close. Vex’ahlia kissed her deeply, the taste of Jester still on her lips. The tiefling smirked into the kiss. She bought her tail up between them. Vex licked her own juices off of it. “Mm, I do love the way I taste.”

“You should, you’re extra tasty. Like chocolate. Although, a bit more like honey. So, do you think your husband has suffered enough.”

“Mm, I don’t know. What do you say, darling? Are you willing to hand over all of White Stone to me just to cum?”

“It was yours from the day we met, love. You know that.” Vex couldn’t help but roll her eyes at that.

“Aww, he’s so sweet” Jester muttered as she put on the leather harness. “So, do you want to lube me up, Lady Vex’ahlia?”

Vex lowered to her knees without answering. She grabbed the lube and slathered some on her fingers. “Rub it into your hands first, warm it up. I can’t really do that.”

“So I noticed. It was, unexpected. Most tieflings are, well” Vex blushed as she trailed off. She didn’t want it to sound like an insult.

“Warmer? Yes. Well, I take after my father in some areas mama always said. I hope it isn’t an issue. It isn’t that noticeable for most of my body, but my tail…” For a moment, Jester was uneasy. She was still relatively new at this.

“Not at all. It’s different, but damn good. I can just imagine how it’ll feel with you and Zahra switching off on me.” She shuddered and continued the sloppy handjob on the dildo in front of her. Once it glistened, she gave the fake cock a peck on the head. “All ready, do you want me to open my husband up for you?”

“Yes please. I was going to plug him, but I thought it’ll be sweeter to see you do it. You two seem perfect for each other and it’s quite adorable to watch a couple in love.” Vex raised an eyebrow at that but took the lube over to Percy.

“Ready for your turn, darling? It’s time to put on a sex show for The Sapphire. She’s a professional, so we better make it good, Percy.” Vex bent down and kissed him. Percy kissed back, but passively. Vex always took charge like this. Her tongue hungrily explored her husband’s. She nibbled on his lip a bit.

Then she stood up and walked to the other end of the bed. She crawled onto the bed til she was between his legs. Without a word she took his cock in one hand and licked from the base to the tip. “You’re so hard for us, baby. I love it.” She looked over at their guest. “Do you want me to make sure he doesn’t finish until you get a turn? I don’t want you to be left out.”

“No thank you, Lady Vex. Just do whatever you want. It is your anniversary, after all. Trust me, I’ll be able to work no matter what. Well, unless he passes out. But then, that’s why I love couples as clients. There’s always two of you. Just make sure he’s open.”

“Oooh” Percy moaned as Vex did just that. He looked down to see his wife had 2 fingers inside of him already and half his cock down her throat. “Oh, Lady Vex’ahila, please, I can’t take much more.”

She pulled her mouth off the cock. “Do you want this, Percy? Well then, beg for another finger. Beg for me to open you up for our guest and you’ll cum as much as you can tonight.”

“Please, Lady Vex’ahila. Shove a third finger in. Fuck, come on, prepare me for the beautiful woman who just fucked you in a way we never even thought of before.” She did so, and took her husband back into her mouth. “O yes dear, that feels so good. Pelor, you could do whatever you want to me. Hell, if you wanted to shove your whole fist up there I’ll let you. Go on darling. Open my butt up for that big strap on. Fuck, I’m so close.”

Vex pounded her fingers in deeper at the same time her nose met Percy’s groin. She smiled best around his cock. He came and she pulled back, using her other hand to keep pumping. “That’s it, make a mess for me, darling. You know you’ll clean it up.” She continued milking him. She chuckled as she removed a strand of cum from her eye. “He’s all ready for you, Miss Sapphire.”

As the two passed, Vex gave Jester a quick kiss. Just enough to give the Wandering Sapphire a taste of her husband’s seed.”Yummy.” The blue woman handled her pink strap-on as if it was real. “Now lift your legs a bit. And try to spread them as much as you can. That’s a good boy.” Jester double checked the ropes to make sure they were still tied and there was no sign of circulation being cut. Then she came closer and lifted his legs a bit more.

She smiled at the slight gape Vex has opened. It was clear this wasn’t Lord De Rolo’s first pegging. “Ready for Sprinkles?” She gave him a look when he just nodded.

“Yes, Miss Sapphire. I’m ready for Sprinkles.” Percy was unable to focus on how ridiculous his words were. He felt the dildo at his entrance. Jester thrust forward and in him. She slowly worked it in and out, going farther each time. Somehow, Percy’s natural curiosity came out. “How long is it, anyways?”

“7 and a half inches. A little on the big size, but nothing obscene. I got most of it in already.” She looked down at his hardening cock. “And you clearly like it.” She slammed her thighs against his.

She looked back at Vex. The Half-Elf was sitting on the chair rubbing her own pussy. Once Jester was sure Percy had no issues taking it, she asked “So, Vex, how do you want me to fuck your husband?” She knew who was in charge here.

“Fuck him fast and hard. He’s always complaining about me teasing him, so give it to him all at once. He’s earned it.”

Jester instantly picked up her pace. She grabbed hold of Percy’s legs again and lifted them up above her shoulders. Percy was a bit shocked at her strength. She also wrapped a hand around Percy’s cock. “Normally, I’ll be worried about this. But your wife here seems to know your limits well. And I bet she uses you like this a lot. You’re so pretty tied up like this, taking a fake cock without any struggle. I know I couldn’t resist doing this every night if I was her.”

Percy blushed. “All she has to do is ask”. He groaned.

Jester continued pounding in and out as she paid attention to his cock. Once he was fully hard again, looked back at Vex. “Can you untie his legs for me, Vex? I want to see what he looks like folded in half taking my cock. I bet he’s even more beautiful.”

Vex was untying the first leg already. “I bet. If only we had someone to draw it.”

Jester smiled. “I can draw a picture and send it when I’m finished if you wish. Trust me, no one but us will see it. Well, and The Traveler.” Vex gave a perplexed stare. “My god, don’t worry, totally trustworthy.” With that Jester grabbed hold of Percy’s legs and shifted him.

Once he was in position, Jester thrusted in again. She was slower, but went more deliberate. Percy was folded up with his own cock inches from his face. He figured out what Jester wanted. He would have begged for it if he had the ability to speak. Instead he moaned and grunted as Jester fucked his ass and pumped his cock.

Vex was a step behind Percy but soon realized The Sapphire’s plan. She bent down and took his balls into her mouth as Jester continued to sodomize and jerk off her husband. The room was quiet except for grunting, moaning, and slurping until Percy came again. He came all over his own face. Vex’ahila quickly bent down, still covered in Percy’s cum. “Let’s clean each other up, darling”. Jester pulled out and watched the married couple.

_____________________________________________________________________________

Later, the three of them were dressed and back in the front room of the mansion. “So, how long will you be staying in Whitestone?” Percy asked.

Jester was back in her black outfit. “Not long, probably another day or two. I need to, well make a tithe as Beau calls it then we’re off to Emon.”

“Tithe? I got to admit, I never heard of your god The Traveler and I doubt there’s a temple. No offense, just the only temples here are for Pelor. Well and the Raven Queen.” Vex had a look of longing at that.

“That’s fine. The Traveler cares less about where you tithe and more how. I usually leave them at brothels.” At their inquisitive looks Jester explain. “The Traveler is a fan of mischief. Nothing overly harmful, just things like a mysterious symbol showing up that a priest at a temple may think is blasphemy or switching around all the signs at a library or a brothel trying to figure out where the mysterious client who overpaid came from. Especially if they’re pretending to be royalty.” She remembered where she was. “Not that I would ever soil your name or anything, Molly usually uses a country no one heard of.”

“Interesting. But why brothels?” Percy asked.

“O, well Beau, one of my bodyguards, pointed out how much money I actually make compared to most of my profession. I just decided that wasn’t quite fair and I had plenty to spare. But I don’t it to seem like I’m taking pity on them or anything, so I usually send Molly or Beau or Yasha (I sent Fjrod once but that seems like a bad idea) as a client who lives a big tip. Although once I left a giant doughnut filled with gold at a brothel in Zadash. That was fun.”

Percy and Vex looked at each other. Percy adjusted his glasses. “Well, you said you were going to Emon? Lovely city. We have a keep and some friends there.”

“Yea. Hey, maybe your next client will be one of them.” Vex went through a mental list of all the possibilities.

Jester looked at them awkwardly “Maybe, although I tend not to name them. A bit of a risk.”

“Yes, I imagine most would be embarrassed if this came out. Not the type of thing most who can afford your services want public.” Percy looked at his wife.

“Buncha prudes” Vex muttered under her breath.

Jester chuckled. “If only that was the worry.” At the blank stares she explained. “Just imagine what could have happened if people knew I was coming here. A complete stranger coming from abroad to meet with the heads of a nation? I’m an assassin’s wet dream.”

Vex laughed at that. “Well, that is a bit of a worry. I’ll have the guards frisk you next time before you enter. Although won’t be the first assassins we fought off.”

Jester left shorter later, a substantial payment in a special compartment of her haversack. Percy looked at his wife. “Well dear, that was most special.”

“That it was.” She smiled as a thought came into her head. “Hey, isn’t Keyleth celebrating her Aramenté anniversary soon?”

**Notes for the Chapter:**

> I hope you enjoyed. I have a few plans for future chapters but if anyone has suggestions on some future clients and their requests feel free. I don't expect this to get updated a lot (as with my other fics) but I am trying to upgrade more frequently in general.


	2. Kima and Allura

**Summary for the Chapter:**

> Kima and Allura decide to spice up their sex life.

Jester, Beau, and Yasha walked through the Cloudtop district of Emon. “So Jess, do you know where we are going? We’ve been walking for an hour around for an hour. I think we’re starting to get looks.”

“It’s called the Ivory Tower, Beau. How hard can it be to find? I’m sure we’ll see it.” Jester pointed at the city around them. “Besides, look at the houses. It’s so different than Nicodranas.”

As they walked, Yasha and Beau noticed someone following them. As Yasha’s hand went to her sword the guard spoke up. “Excuse me, miss, are you three looking for something?”

The guards with him all eyed Yasha. Jester looked around. “O, yes. Do you know where the Ivory Tower is?”

“I do. What is your business there?” While the guards calmed down as Yasha let go of the sword, they were still on edge.

Beau spoke before Jester could. “Arcanist Allura Vysorsen has requested her service, for a, um, personal matter.” She pointed at Jester, the most well dressed among them in her usual green cloak.

“And you two?” Beauregard was wearing a jacket over her usual clothes and Yasha was in her usually hides. Neither looked at home in the richer area of town.

“They’re my friends.” Jester said quickly. “And my bodyguards.”

Satisfied with the explanation, the guard directed them to the Ivory Tower. Beau spoke up. “I told you we’ll stand out.”

Jester just chuckled. “Yes, well we always do. But come on, I need you two here. While mama doesn’t think anything bad is going to happen, she never met these clients before. And I’m going be tied up. And gagged.”

Yasha blushed at that. “Jester, if you don’t feel safe” she began before being cut off.

“I feel plenty safe. Any red flags and I don’t accept the job. I made that promise to mama. But you never know. There’s a reason mama keeps Bluud nearby. Plus, getting lost in a moment of passion can be just as dangerous as anything. You and Beau just need to run in if you hear me safeword or something. I should be able to move my mouth enough to cast thaumaturgy. Between you guys and The Traveler always watching, I’ll be fine. Ooh, is that a bakery? We got to try that on the way back.” 

The trio walked up to the white tower and knocked on the door. A few moments passed before a tall human woman with blond hair and a blue dress answered. “Hello, you must be The Wandering Sapphire. I am Arcanist Allura Vysorsen, of the Tal’Dorei Council, please come in.”

Yasha and Beau straightened up as they followed Jester. “Please to meet you. I’m Jester, and these are my guards, Beauregard and Yasha.” Allura guided them into the room.

A halfling with darker blonde hair, tan skin, and a scar over her eye greeted them. “3 of them, Allie? I know we wanted to experiment but…”

Jester saw that Kima was a bit nervous. “You must be Lady Kima. I’m Jester, the Wandering Sapphire. Don’t worry, these are just my bodyguards, Beau and Yasha.” Kima saw Yasha’s sword and calmed down.

“Ah, I guess that makes sense. You two see a lot of action?”

Yasha blushed. “Well, um, this is the first time Jester asked us to um supervise a client but it’s not like we’ve never”

Beau nearly face palmed. “I think she meant with my fist. Or your sword at least. We came across a few bandits right after Whitestone but nothing much.”

Kima nodded and began talking with the two guards about the fight. Allura frowned and pulled Jester aside. “Supervise? I wasn’t expecting to be watched”

“O, don’t worry. They don’t need to be in the same room, just right outside the door. Or I have a few curtains in my bag we can use if there isn’t a door.” She patted the pink haversack. “I do not mean to offend, Lady Allura, but your wife and yours request will put me in a vulnerable position. And you two came without any recommendation from mam, I mean Marion, the Ruby of the Sea or any of the local guilds around her.”

“Well I guess that makes sense. We haven’t really done anything like this before but we thought it would be fun. But Kima and I both agreed we both needed to be in charge of the situation to avoid any thought of jealously and stuff.”

Jester had the biggest grin on her face. “That’s real sweet and makes perfect sense. Communication and knowing both your partner’s boundaries and your own is key. Don’t worry, Beau and Yasha are just here in case things get out of hand. You won’t be the first clients who didn’t notice a safe word or a hand signal because the scene was too damn sexy. I mean, you’re going have me all tied up and gagged while you two have your way with me. And I look forward to it. But just in case my cute little body distracts you from noticing something, I need Beau and Yasha nearby to communicate to. I should be able cast thaumaturgy” at that a window across the room opens “with a gag in. As long as you don’t tie me up with anti magic cuffs.”

Beau and Yasha heard that and looked over. The three shared a somber look. “So, how exactly do we do this?” Kima asked. She sensed the silent conversation between the three was best left silent. 

Jester perked back up at that. “O, well first there is the payment we’ve already talked about. Then we’ll go over safe words and what is expected and everything. I assume we’re going to another room?”

“Ah yes.” Allura passed a large purse filled with gems and gold to the tiefling.

Beau spoke up as Jester counted. “This bag isn’t magic, is it? Not a bag of holding or anything like that?”

Kima frowned at that.“No, it’s just a bag, why? The messages back and forth didn’t say anything about magic.”

“It’s just to avoid opening a rift in the dimension, dear. I told you a thousand times never to put a bag of holding inside a bag of holding.” Allura put a hand on her wife’s shoulder.

“Wait, that’s actually a thing? I just thought you and Drake didn’t want to end up with 8 bags inside of each other and forgetting which one had the thunder potion or whatever.” Her wife laughed at that.

Jester finished counting and took out most of the gems. She placed them in a special pocket of the haversack. The rest of the payment went into a different pocket. Allura heard a small poof. “That isn’t just a pocket dimension in there, is there? That sounds like a small teleportation circle.”

“It’s so cool. Widogast’s Teleportation Pocket. A friend of mine made it before we parted ways in Nicodranas. Can only teleport nonorganic matter or something. Just in case a bandit gets lucky.”

“That sounds interesting. How exactly did they get the spell to work inside a pocket plane like the haversack, that would cause the same feedback loop…”

Kima tugged on her wife’s arm. “Allie, you’re talking shop.”

“Right, sorry. Follow us upstairs. Carefully, you can get a bit lost.” The three followed. Allura conjured some chairs for Beau and Yasha as she led Jester into the room.

Jester looked back at her friends real quick. “Just remember, if you hear Hupperdook or the door slams open rush in.”

Yasha just nodded and blushed. “You can trust us” Beau confirmed.

“I know.” Jester looked around the room. “Well, this is unexpected.”

Kima rolled her eyes “And what exactly did you expect? A bigger bed with gold entrusted tapestry everywhere and pillows worth their weight in platinum?” She was used to other council members flaunting their wealth.

“Actually, I was expecting it to be more of a sex dungeon. A hitching post somewhere, some manacles showing, and those toys your request mentioned displayed all over. This is clearly not your bedroom.” Kima raised an eyebrow. “That bed wasn’t slept in for at least a week and there is nothing really personal here. Plus the path to get here was too long for regular use. I mean, I understand. A lot of people keep a separate room for the less orthodox pleasures.”

Allura fiddled with a chest at the front of the bed. “You know, that wouldn’t be a bad idea. I bet Kima would love that. But this is just a guest room. However, this chest is connected to a few others” Allura muttered a quick spell and began pulling this out.

Kima laughed. At her wife and Jester’s looks she explained. “Sorry, I was just picturing Highbearer Vord walking into a sex dungeon instead of his guest room in the middle of the night. I bet he’ll look for other places to stay whenever he’s in town then.” Jester giggled at that. She knew The Traveler would have approved. “So, do we just begin?”

“Actually, if you don’t mind I would like to inspect the instruments you want to use.” Her tone made it clear that this wasn’t a request.

“Of course.” Allura was already digging out a selection items. “Honey, which ones did you want to use?” Kima gave her a looked as if they went over this before. “What, it’s your collection. I barely know their names.”

Kima walked over to help her wife. “You like using them on me well enough.” She bent down and kissed Allura’s cheek before digging through. “Let’s see, where are you? Mm, this can be a warm up.”

Jester looked at the thick green dildo came up and grinned. “Ooh, is that a half-orc? That knot is so detailed. I can never find one that does it justice.”

“Yes, it’s named Matuk. And it pulses and twitches as if it’s real.” Jester gasps as it wriggles in her hand. “It can even cum. Requires a magic word so never too early, better than the real thing.”

Jester fondled the toy in her hand. “I don’t know about that, but whoever made it should be proud. My supplier can just get them to vibrate and considers that a feat. When I asked for a knot she just gave me one that widened at the base. I swear, that old lady never saw an orc naked.”

“Gilmore has plenty of hands on research there. You should check his shop out, Gilmore’s Glorious Goods. Just say I sent you, and that you’re looking for the sex stuff. Otherwise he’ll try to sell you an axe or something.” Kima pulled out another toy. “Mm, this is a possibility.” She throws up a red cock that almost came to a pointed tip.

“O, tiefling. Nice.” She grabbed it. “And it’s heated. Nice touch. Kinda big though, I take it your wife enjoys that?”

Allura measured out some rope as she sighed. “Not particularly. Kima’s the ‘size queen’ as she so eloquently says it. She’s surprisingly, um, flexible I guess.”

“Yup. I like them big. And artificial.” The giant platinum colored, scaled dildo she pulled out next emphasized Kima’s point.

“Mm, that’s isn’t a dragonborn, is it? But it’s beautiful. What’s it’s name.”

Allura rolled eyes. “She calls it Bahamut.” Kima playfully punched her. “What, you do. Now I wonder what the Highbearer will say about that form of worship.”

Kima raises an eyebrow. “Well you can always ask him next time we’re at a stuffy dinner. It’ll liven the room.”

“O, you worship Bahamut? I always thought his followers were a bit stuffy. If I knew you could be this fun I wouldn’t have drawn dicks all over… Hey, have you ever heard of The Traveler? He’s my god, but not very people know of him. He visited me in my bedroom when I was a lonely kid and always been there for me.”

“Your god visited you? When you were a kid? In your bedroom? Um, are you sure he was a god?” Allura asked hastily. She had heard some rumblings of a new cult, but nothing to give her too much concern.

“Well, if he wasn’t a god could I do this?” A bunch of sparkly pink hamsters with unicorn horns swarmed around the tiefling.

“Certainly looks divine to me.” Kima poked one of the hamster-unicorns. “So, do the toys meet your approval?”

“O yes. Mm, And that rope seems perfect to tie me up tight without cutting off the circulation. But the message from the Lavish Chateau mentioned a gag? Can I see how it fits and feels first, gags can be tricky.”

Kima tosses a small belt at her. “Here, knock yourself out.” Jester fiddled with it a bit. Like the rest of the couple’s toys, it was finely crafted. She examined the small ball that was clearly going in her mouth. It seemed normal enough, although the ball flattened out on the other side.

“Is something supposed to go here? And these markings look magical.”

Allura saw a tiny bit of concern on the tiefling’s face. “Ah yes, that has the same enchantment as my harness.” She showed the leather belt and grabbed the half-orc dildo. She placed the base to the middle and the slot expanded a bit and the cock was attached. “Although this one also has a sensory enchantment on it so the wearer can feel it as if it was their own flesh.”

Jester’s eyes lit up. “I certainly need to visit Gilmore’s. That can make things a lot more interesting. I bet even The Ruby of the Sea would want one.” She finished inspecting the gag.

“Now we need to go over safe words, limits, and etiquette. As I’m the one being tied up, this will mostly be about me but also both of you may get uncomfortable during this. If you do, there is no shame in letting us know so we can either take things slow or stop altogether. My safe word is Hupperdook. If I say it or if you think I say it (although really, Hupperdook is such a specific word it is hard to mistake, which is part of why I picked it). The requests you sent doesn’t seem to be anything close to a hard limit, although is there anything you didn’t mention in this list you may be interested in?” She point to a large piece of parchment and looked it over. “I see here you don’t mention anything about impact play, spanking, or choking? It’s totally find if that isn’t you thing, it’s just something I would prefer to not be surprised by and often comes along with bondage.” Jester rushes as she spoke to get the entire thing out before Allura could answer with a barrage of questions. She found she usually covered most of them if she could just get through the speech. “Also, feel free to mention anything you like, don’t like, or flat out refuse although Lady Allura seems to have been thorough”. She again looked at the message.

Kima came up to read over her shoulder. “Wow, how many sendings did it take to send that? Mm, toys, rope, fisting, anal, oh really Allie, you said ‘sharing of the professional’s oral facility as she provides the customers with physical pleasure’?” She kissed Allura quickly. “You’re adorable. Mm, she seems to cover all the basics. Although that minx will probably go after those tasty looking tits of yours too. She’s a bit of a biter with those, but not enough to leave a mark.”

Allura blushed. “Well, they do look lovely. Also, um, me and Kima aren’t sure how we’ll react to kissing someone else or seeing our wife doing it. It may seem a bit trivia with what we are about to do but”

Jester cut her off. “I understand. Different acts have different levels of intimacy for everyone. I’ve had one couple where someone just watched and felt that if they had sex with me it’ll be a betrayal as I banged the hell out of their partner. Others kiss me on the mouth the second we’re in a room together. Trust me, this is supposed to be enjoyable so whatever you’re okay with. Now, are we ready to start?” Jester took off her cloak in preparation.

“Almost, I just need to get 1 thing out.” Allura cast a spell and a small black padded table with a few cuffs on them appeared.

Kima was still reading the written down requests. “Hey, why is there some added writing to this? Looks like scribbles.”

“O, yea, ‘light humiliation-emphasis on naughty name calling.’ Calling me a ‘dirty little slut’ and stuff like that. Your wife called it ‘humiliation’ but I had to get her to be more specific. The stuff people want to call me or be called can get pretty out there. I once had a guy call me an evil demon spawn, and that just got awkward without any fun roleplay talked about beforehand.” Jester realized she was babbling by the look on their faces. Kima was lost and Allura looked ready to write an essay on the subject. “Anyways, how do you want to begin?”

“Strip”. The blue professional obeyed Allura. As she did, Lady Allura approached and took the clothes. She folded them and put them off to the side of the room.

Jester smiled. “Thank you.”

“On your knees, slut.” Kima was already naked on top of the table. Her legs were already spread and waiting.

“Go on, pleasure my wife. I’ll join in a minute.” Jester crawled over to the table. The tiefling moved quickly between the bronze halfling’s legs.

“So, do you want me to tease you slowly on the edge or” before Jester could finish her question Kima grabbed her horn and guided the blue head between her crotch. Allura giggled at her wife’s impatience. Jester took the hint and began licking. 

“Lady Kima, where are your manners?” The wizard kissed her wife.

“When did I have manners?” She moaned as Jester picked up the pace. “Fuck, she’s good Allie. I mean, she isn’t you but, fuck”.

Allura glided reached down and glided her finger along one of Jester’s horns. “Well that is what we hired her for. A little slut for both of us to enjoy.” She took a firm grip of the horn and gently tugged. Jester quickly moved between the human’s legs. “Right there, that’s it.”

The Wandering Sapphire kept eating whichever cunt was in front of her as the wives passed her back and forth. Soon Kima laid on the table moaning with Jester’s blue head between her legs and Allura switching between the halfling’s breasts. “Fuck, come on Allie, just a little more. Please, let me cum all over this slut’s face. That blue adorable face of hers will look so hot covered in my juices.”

Allura lingered on Kima’s nipple as she savored the look of pure need on her wife’s face. “You heard her. Go on, Jester, make my wife cum.” At those words Jester sped up. Kima was already close. Allura moved down and shoved the traveling concubine’s head even deeper in. Kima moaned as she finally came. Allura whispered into Jester’s ear. “She tastes great, doesn’t she?”

“Tasty” she said from between Kima’s legs. The halfling rode out her orgasm with the tiefling’s help. Slowly Kima came down off her high. She looked down and saw the blue face covered in her juices. “How do I look?”

“Fucking hot.” 

“She’s right.” Allura bent down to lick Jester’s face. “Mm, delicious. Now get up, sweetie. That’s where Jester’s going.” Kima got up quickly and sat on the guest bed.

“Take your time prepping her for your big plan, Allie. Enjoy this, no need to rush to the end.”

Allura walked over to the table and started fiddling with the different straps and cuffs. “I will, Kima. Besides, looks like you can use the break.” Kima rolled her eyes but watched eagerly. “Now come here, Jester. Lie down.” She cuffed Jester’s hands down to the sides of the table near her head. “Is that too tight?”

“Nope. Perfect” Her arms jiggled for emphasis. “Oooh.” She was surprised at the sudden attention to her breasts. Allura just smiled around one of Jerster’s dark blue nipples. “Thanks for the warning, Lady Kima.”

Kima chuckled a bit from the bed. “Brace yourself. My wife can spend hours worshipping a gorgeous pair of breasts.”

“You won’t hear me complaining. She certainly knows what she’s doing.”

Allura continued sucking on the hardened nipple before switching to the other. She licked, sucked, and playfully nibbled on the full breasts in front of her. Her tongue glided all over the blue mounds. It dipped between the two before climbing up again, the wizard memorizing every inch of those tits. Jester just moaned at the attention, unable to grab the council member’s head to make sure that mouth lingers just a little bit longer before moving on to the other breast.

Kima watched for as long as she could. “Aww, darling, I think the slut wants a little more. Hear that, she’s practically whining like a puppy now.” Before Jester could retort she felt the gag on her lips. “Open wide, slut. There, that’s a good whore.” Kima tightened the gag around Jester’s head. “There, is that good?” Jester nodded.

“Imm goooooooooo” Jester muffled out from behind the gag.

Allura finally took her mouth off of the blue tits. “Perfect, that should be enough for her to cast a cantrip. Now, Kima, do you want to add the attachment already? I could work around that.”

“Nah. I think I’ll still watch for now. My cunt is going be sloppy after watching you fuck this slut and stretch her out.” Kima returned to the bed. “Besides, I know you love watching me fuck myself, Allie. Just give me reason to.”

Allura moved down the table and grabbed Jester’s leg. “Here, spread it just like this. I want access to both holes.” She grabbed the rope and tied Jester’s legs to the table. She took a step back to just look at Jester gagged and tied to the table with her legs spread open. “Beautiful. And look, Kima, she came already plugged.”

“Smart girl. Bahamut knows you’re going do your best to open that hole up. I had to grab extra lube just out of fear of what you’ll do with another ass to fuck.” Allura rolled her eyes at the ribbing.

“Sure, make me out to be the one obsessed with tits and ass. As if you don’t have your own kinks.”

Kima gave a mock horrified look. “Me? Kinky? Why, you would think I just paid an absurd amount of money just to tie up some helpless girl alongside my wife.” Her look broke with a laugh. “Come on Allie, I love how much you appreciate the female figure.”

The wizard shook her head. “You also love giving me a hard time about it.” She blew her wife a kiss. “But then, that is why I fell for you.” She turned her attention back to Jester. “What do you think, honey? Should I leave it in and go slow, warm her up?”

“Take it out and fuck that ass.” Kima’s fingers were now between her own thighs. “She’s slopping wet already. Use Beezle for it though, Matuk will destroy that fuck hole way too soon. Plus you can use it later.” Allura took her time putting the harness on. She grabbed the big, red cock with bumps around it and held it to the harness. The material shimmered pink as the dildo attached itself.

Allura then grabbed the small green ring at the end of Jester’s butt plug. “Mm, nice and easy.” She slowly began to pull plug out before pushing it back in. She fucked Jester for a few minutes with the plug before removing it with a final twist. “There, opened up just enough for some fun.” The wizard spread some lube around her fake cock before placing at Jester’s asshole. She nearly whispered “are you okay?”

Jester eagerly nodded. Louder, Allura spoke “Your slutty little whore ass is going enjoy this, slut.” She was slow but steady, thrusting the cock into the tight hole a few inches at the time. Allura grunted as the dildo’s magic worked. “Fuck, your hole feels so good.”

Eventually Kima got too excited to keep to herself. She was holding the giant platinum colored dildo. “That looks so good Allie. You’re fucking that slut ass. Do you mind stopping so I can use her mouth?”

“Of course, honey. Besides, seemed to enjoy the knot so much I think we should give her a test drive.” Jester tried to see what was going on but it was too much. She saw Kima approach her and held the base of the large, scaled dildo to the bald gag. Up close, Jester would have thought it was actually the size of a dragon’s cock. It attached to the flat side of the ball gag at the same Allie attached the second cock to her harness.

“Mm, she looks more than ready.” Jester looked back at Allie. The large, knotted orc cock was position on the same harness as the one that been plowing her ass.

Jester couldn’t help but muffled out “fuck me” at the sight.

“Hear that, Allie. I think we found the perfect whore for you. She wants you to fuck both her holes while she watches me fuck myself on this giant dragon cock.” Kima stood over Jester’s head, positioning her cunt right over the dildo. She waited for her wife to get into position.

Together, the two women moved. Jester’s ass and pussy were filled at the same time Kima lowered herself down. The two women wasted no time. They were both too eager to fuck the blue tiefling tied up beneath them to take it slow.

Jester moaned around the gag as Allura fucked both her holes. She savored the unique feeling of two cocks being thrust into her by a single person. Her ass was once again filled with that long, hot tiefling cock while her pussy was knotted. She was used to both feelings separately, and even been double stuffed enough times to know how that felt but this was different. With a single thrust each hole was filled, and only one person had to pull back for Jester to feel empty.

All the while, she watched the small form of a halfling slam herself down onto the cock coming out of her mouth. “O Allie, this is so good. Fuck, Bahamut, so big. Fuck.” Jester thought the halfling was splitting herself in half for that pleasure. And she couldn’t blame her. The two cocks inside of her were bigger than most of her clients and Jester wanted more.

Allura went faster and faster, too focus to even curse. The harness meant that she felt both of Jester’s holes as they fucked. She reached forward and grabbed Kima’s tits from behind. “Fuck, Allie, that’s it, fuck this whore while I fuck myself all over her face. Fuck, Allie, I love you so much. Fuck!” At that moment Allura kissed Kima’s neck as she kept fondling her tits. All three women came within seconds of each other, Jester unable to anything but take it.

The tiefling couldn’t even smile as she watched the wives make out over her body as they drove each other on to another orgasm.

As Kima and Allura came down from their pleasure soon the wizard panicked. “O no, o no, Hupperdook, Hupperdook, damn it, help someone.” Kima looked at where Allura was pointed at and Jester’s body. Before she could explain to what happened, Yasha and Beau were in the room.

“What’s wrong, what happened?” The two body guards were on high alert.

“I don’t know, all was going fine but I guess I must have been going too hard and not notice a sign or something and she passed out, I think I saw her eyes roll back. She could be having a stroke or something. Kima, get that gag off her, check if she’s breathing.”

Beau burst into laughter. Kima quickly joined her as well as Yasha bent down to check. “What’s so funny? I mean, I didn’t mean to hurt her or anything.” Yasha took the gag off Jester and gentle caressed her cheek. She had experience with this.

“Hey, Jess? Hey. Good time, huh?” Jester opened her eyes and saw the panicked look in Allura’s face.

“O fuck. I haven’t been fucked that well by a client in months.” She looked around at the rest of the room. “Um, Beau, Yasha, why are you here?”

Kima answered that question. “Sorry, my wife is not the most experienced when it comes to sexual partners. I think you’re the first woman who passed out on her. I got a bit more stamina than most. Although I’m a bit of a squirter. Allie just thought you were in danger and called in your friends. Either that or she wanted to show off our toys.” She looks over at her wife once again. “It’s fine, Allie. You banged her so good she fainted. It happens sometimes, especially after multiple orgasms.”

Allie began to blush. “Oh, that makes sense. The process of an orgasm can take a lot out of the body, especially multiple ones in such a short time. Um, sorry for”

Jester interrupted her. “Nothing to apologize for. You thought there was a problem and you got help. Thank you. Besides, I haven’t had a client make me pass out in months. Trust me, this was my pleasure.” She was sipping on some water that Beau passed her.

As the body guards left the room Beau gave a confused Allura a high five. “Good job, trust me that isn’t an easy feat”.

The Wandering Sapphire and her companions made small talk as they cleaned up and got dressed. Jester asked some questions about Gilmore’s shop and the city as she tried to ease Allura’s embarrassment. As she left she gave them a small business card to contact her again.

Jester, Beau and Yasha soon departed the tower. It was still late afternoon. “So where to now, Jester? Want to just rest up at the inn? We can take care of your tithe tomorrow.”

Jester just smiled. “Nope. Let’s go get Molly, then we’re going shopping. Kima told me of this awesome store.”


End file.
